Figure It Out On The Way
by zemarha
Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.
1. The Feeling Is Familiar

Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: Set sometime after Sookie's wedding, but well before the dance marathon. I've got a couple (short) chapters ahead already written, but I'm missing a bridge between this one and part III... so until I can figure that out, feedback is definitely appreciated!

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I. The Feeling Is Familiar

In my experience, things never really go the way I plan for them to. I think I've learned to expect that. I know I can't control the way the cards fall, so sometimes I put forth some kind of effort and sometimes I don't bother. Either way, I try not to worry about it too much. I know I can't count on stability, or routine, or getting what I want- but I can count on me. I know who I am and I know how I feel about things. I know what's possible for me and I know what's not worth my time. I _don't_ know where I'm going. I figure, as soon as I pick a place, it'll immediately be taken out of the running for me. It's less disappointing to just not go after things at all, for the most part. To just roll with punches.

Liz happened. Robbie and Jake and getting busted and a night in jail happened. Stars Hollow happened. Rory Gilmore happened.

Rory Gilmore. And suddenly all the things I thought that I knew about myself started to crumble a little bit. Started to fray at the edges.

She made me want things I shouldn't have wanted. She made me feel things I wasn't expecting to feel. Made me go after those things. Things that I never really had much chance of getting in the first place.

She confused the hell out of me. I'm not used to feeling uncertain. I'm not used to wanting things I can't have- I'm usually smarter than that. I'm not used to worrying about what someone else thinks of me. I'm not used to trying to impress someone.

I'm not used to caring like that.

But Stars Hollow happened, and Rory Gilmore sure as hell happened, and I guess I just did my damnest to keep my head above water and deal with all the unfamiliar feelings.

And eventually things started happening. We moved forward. It wasn't always exactly how I pictured it happening; it wasn't always easy. But I thought we were getting closer to some semblance of a happy ending. Or if not a happy ending, at least a valiant attempt at a good start.

Somehow, unreal as it seemed, things appeared to be going in my direction.

Well, more or less my direction. I made her laugh. I held her interest. I think I made her sense on some level that there was so much more out there than her small town life- things that would excite her, things that might scare her, but above all else things that would make her feel _alive_.

And then I crashed her car. I left her, and I left any ideas I had of making plans and finally, _finally,_ getting what I wanted.

But she sought me out. So I bought her lunch, I took her to a record store, and then I followed her back to Stars Hollow.

And she kissed me. And welcomed me home. And made me hope. Made me think I had a shot in hell at love with her.

But she's always been easily frightened. She's always been a runner, whether literally or just in her head. She's never been great with going after the things she really wants, as much as she keeps up this pretense of being ambitious. And as soon as the things she truly wants can't be guaranteed- forget it. She'd rather stay cocooned in what's safe and stable and right there in front of her, than chase after something that could be so fucking amazing- but could also turn out to be nothing.

Rory Gilmore may have wanted me, but she was never strong enough to do anything about that.

And in my mind that's always translated to something more along the lines of: She didn't have enough faith in me for it to be worth it. I was never really good enough for her.

Maybe all of our shortcomings can be explained by the way we grew up and the insecurities we carry with us. Maybe her father never being in her life has made her unconsciously seek the kind of normal, ordinary stability she missed out on as a child. Maybe growing up with a mom who could never really care for her son left me forever doubting my self-worth; doubting that anyone could ever see anything worth loving in me.

Regardless of the reasons or the psychoanalytical breakdown, somewhere along the path of our twisted relationship- if you could really even call it that- confusion turned to anger.

She did what Rory Gilmore does- she ran. She left. Without a word. For three months. And when she came back, she was still with him. Still living her fairy tale fucking life, without a single shred of concern for what she might be doing to me.

Because people like me obviously don't factor into lives like hers. And I knew that. I really did. But somehow, at some point, she had me banking on impossibilities.

God damn her. For making me hope. For making me want to love again, after so many fucking failures.

Jess Mariano, hope, and love. Things that _don't_ go together.

And so this, at least, is a feeling that I'm familiar with. I remember angry. I know how to deal with angry. I know what angry means and where it usually takes me. The sadness that's mixed in, well, that's not as familiar... but I'm doing my best to block that part out and focus on just the anger.

It's not what I want. But I try to keep reminding myself not to want things I can't have anyway. I used to be good at that. I'm sure I can relearn that skill. Learn how to bank of the few things I can count on again.

So fuck Rory Gilmore. If she's ready for something more, she can go ahead and go after it and see what happens, no guarantees. And if she wants to stick with the fairy tale and never step out into the unknown, then that's her fucking choice.


	2. One Foot In Front Of The Other

Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: This story switches back and forth between Jess's POV and Rory's POV... that should be fairly self-evident, but just in case, there you go. Also, sorry for the super short chapters- it's not really intentional, just happening that way. There's also gaps in between the chapters- things that have happened that haven't necessarily been fully detailed in the story. Jess or Rory will refer to them, and the rest should be pretty easily inferred, but if it's too confusing tell me (because to me, it always makes sense :P). Last thing, Rory's referring to the scene between her and Jess from Haunted Leg, minus the Shane parts, because in this universe Shane never happened. And as always, any type of feedback is very much appreciated. :)

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II. One Foot In Front Of The Other

_Deep breaths, Rory, deep breaths._ I'm currently standing outside Doose's and trying very hard to not hyperventilate. My palms are sweaty, my heart is racing, and I'm starting to feel a little light-headed. My fight-or-flight instincts are quickly drowning out any rational thought I may have previously had.

Dear lord, why am I doing this again? I could very easily just turn around and walk away and leave this near-panic attack behind, and maybe I could just stop by Luke's instead. Yeah, a nice cup of coffee, a little sugar rush, that'll help calm me down, help my heart stop palpitating.

Oh right. Luke's. Jess. The reason I'm here in the first place. Dammit.

I close my eyes and just think about him for a minute. How shocked I was to see him at Sookie's wedding. How _good_ he looked. How I couldn't seem to stop myself from reaching out to him... and god, how _amazing_ it felt to finally kiss him, to be that _close_ to him... but that was three months ago.

I flash forward to Jess from earlier this week- the Jess who called me out on my cowardice; the Jess who yelled at me for, essentially, leading him on. How his voice had held such a mix of hate and contempt and _hurt _when he asked me if I was still with Dean.

I've always known that Jess has a tendency toward the... intense... but I never imagined that that much anger would be directed at _me_.

But Jess has never led me to believe he'd coddle me. He's never put up with any bullshit, from me or anyone else in this town, and I guess he wasn't about to start now. And as much as seeing that kind of resentment in his eyes _hurt_, now that I've had a chance to get over the initial shock, I think I'm realizing that I need a little bit more of that in my life. Someone who doesn't idolize me. Someone who knows I'm not perfect. Someone to tell me when I'm being an idiot, and not let me get away with anything. Someone to hold me to a higher standard.

Because sometimes it feels like everyone in Stars Hollow is so busy expecting me to be perfect, they're never able to see past that. I'm a one-dimensional character to them, incapable of flawing. Either that, or it's just that no one ever has the guts to tell me when I'm wrong. I don't know how I'm ever supposed to _grow_ if I'm always allowed to keep being status-quo-Rory.

So yeah. Jess's diatribe in the market managed to wake me up a little. I've been... just, so unfair. To both him and Dean. And I guess to myself, to some extent, as well. His words managed to shake me up a bit, and at the very least got me re-evaluating the course I had been set on.

And that brings me back to the sidewalk outside Doose's.

Okay. I can do this. Big deep breath; one foot in front of the other; ignore the crazy-erratic-thumping thing in my chest, and push the door open. Slow, steady steps toward the checkout counter.

"Dean? We need to talk."


	3. For Better Or For Worse

Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: Some actual R/J interaction in this chapter- huzzah! And more to come in the future, I promise. :) And... review please! Even if it's just to point out grammar mistakes or spelling errors, I promise it'll make me happy! :P

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III. For Better Or For Worse

"Dammit Jess! You can't just go through life hiding from all your emotions, hiding from relationships, hiding from any kind of _meaning_ that might exist between you and another person! If you're angry, you have to tell me why you're angry, and give me a chance to explain my side of things. If you're hurting, you should let me try to be there for you. If you're happy- if I make you happy at all- god, you should shout it from the rooftops! Make it _real_! Don't you _want_ to?"

She stops and gives half an exasperated sigh. She's looking down now, and I get the distinct feeling she's just switched from frustrated and angry to very, very sad.

I probably should have been expecting that. Fuck, I was the one who wanted her to _do_ something, to take some action, and she actually rose to the occasion. She broke up with Dean, and she wrote me a letter. Jesus, that letter... just thinking about that makes my mind wander off track... I swallow hard and focus back in on the girl on front of me.

"Because when you don't say _anything,_" she continues, softer now, tracing patterns onto the wooden slats of the bridge, "I start feeling like maybe I don't know you as well as I think I do. Like maybe I've got it wrong. And maybe you don't really feel the same way about me as I do about you. Like maybe I'm not... maybe I'm not good enough for you."

Idiot that I am, I just stare at her. She's blind-sided me – how could she possibly think that? Actually think for even a second that _she_ might not be good enough for _me_? Jesus, if anything, it's the other way around- I'm the one who's not good enough.

Fuck. She's crying. God dammit. Everything about this situation is screaming 'Get the fuck out, Mariano!'. This is so completely out of my comfort zone. I'm not the guy who sticks around for the emotional fallout in _any_ situation. I have _never_ been that guy.

But fuck if it's not different this time. Some part of me knows she's worth it. And I know I'll stick around and see myself through this, for better or for worse. Because clearly, for god knows what reason, she's trying. She's plucking up her courage and stepping out of her shell. Out of her safety net; out of her role as town princess. She must have known what the consequences would be, when she decided to end things with Dean. She must have realized on some level what it would mean if she immediately jumped into something with _me_, of all people, right after that. What the town would say. What her mother would say. I imagine even Lane, try as she might to be supportive, wouldn't be able to completely hide her shock.

And god, that letter. Rory Gilmore is seriously putting me to shame right about now. She's done so much more than I thought she would. She's putting herself out there, and I know from experience how _painful_ that can be- to tell someone things that are so inexpressibly close to your heart, and have to wait for them to respond.

When she walked into the diner and handed me that envelope, without saying a word, I had no idea what she was thinking. All I could tell was her face was nearly expressionless- like she was trying hard to keep it that way- but underneath the mask was a hint of nervousness mixed with hope. A little glimmer of anticipation in her eyes.

But maybe I'm just saying that now, after the fact. Either way, there was no way I saw the contents of that letter coming.

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"_Luke," he calls out to the kitchen, "I'm done out here, I'm heading upstairs."_

_Luke catches the implied question- do you need anything else- and wonders at his nephew's communication skills. Part of him knows that Jess saying _anything_ (and not just leaving) is definitely an improvement, but the other part of him wonders when the kid is ever going to learn to simply say what he's thinking and open up a little._

_Regardless. He seems to be staying out of trouble, doing okay in school, has maybe even mellowed out a bit. And Luke isn't going to push him. He's changed a lot already, in the short time he's been in Stars Hollow._

_So Luke replies, "Okay. You're helping me open tomorrow, right?"_

"_Yeah."_

_Jess takes the stairs up slowly, his mind resting on the plain white envelope nestled in his back pocket. He's wondering what she's thinking, where they might be going from here, because he's heard Miss Patty and Babette whispering about The Breakup, and so he knows his words from Doose's the other day must've made some kind of impression. He winces, remembering how harsh he was with her, but he doesn't regret it. She needed to hear it._

_He's reached the top by now, and he makes his way over to his bed. He's left with no other excuses not to open it, but if he's honest, he'll admit that the whole thing is making him a little anxious. He'd wanted her to be proactive, to go after the things she wants, but now he's not so sure he really wants to know. What if she's not interested in him after all? Could he handle that- not just a vague, "I'm still with my boyfriend", but a clear, resounding, "I don't want to be with you"? In writing?_

_And even if she does want him, even if he's been interpreting their unspoken dynamic correctly, can he handle _that_? He's never tried to make someone else happy before. He thought he'd be able to at least try, for her, but now he's not sure it'll be enough._

_Ridiculous. He's being ridiculous. He should just open the letter and go from there. All this introspection and second-guessing is so not him._

"_Jess,_

_You asked me if I called you while I was in Washington. I didn't. I picked up the phone so many times, but I never got past the first two numbers before talking myself out of that._

_You asked me if I wrote to you at all, and I actually tried that, too. This isn't the first piece of paper I've written a letter to you on. But they all sounded hollow and inadequate and just- not right. I couldn't ever finish them._

_So no smoke signals or fruit baskets, but a lot of almost-phone-calls, and a few unfinished letters._

_I would try and explain it to you, but honestly, I'm not sure I know myself what's been going through my head. In Washington, I just felt... trapped. Unsure of how to fix things. And scared, I guess, too. You're so far from what I'm used to, Jess, and half the time I'm around you I feel like I don't know what the hell I'm doing._

_Just to be clear though, I did know what I was doing at Sookie's wedding. That's not to say I had been planning on that happening- I mean I wasn't even planning on _seeing_ you- but I don't regret it. You probably think I do, but I don't. I regret being with someone else when it happened, but I don't regret it happening. You showing up- you caught me off guard. No one else has ever been able to throw me that off track- I literally forgot everything else, the wedding, Dean, my mom, all of it- and I just wanted to be close to you. To feel your lips on mine. I've never kissed someone and had it feel so _right_. Even if the circumstances were all wrong. _

_Anyway. I'm not sure what the point of this letter is, except to tell you that I've been kind of confused recently. I know that's not an excuse for ignoring you all summer, or an excuse for cheating on my boyfriend, or an excuse for not listening to myself. But I'm working on it. And I'm not going to keep hiding behind what's easiest and what everyone else expects me to do. I guess I couldn't imagine telling you all of this to your face, so... I'm writing it down. Lame as it sounds. And this letter kind of feels just as hollow and inadequate as all the ones before it, but it's the best I can do right now. Hopefully you can understand that._

_-Rory"_

_

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_  
So I pull myself together, and focus, once more, on the girl in front of me. I take a step towards her, and I sit down next to her.

I'm not going anywhere.


	4. So Totally Worth It

Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: My self-esteem depends on your reviews. Well, not entirely, but it sure does make my day brighter when I read your kind (or not so kind) words!

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IV. So Totally Worth It

He didn't profess his love for me. He didn't pull me into his arms and rub my back and whisper sweet, calming nothings into my ear while I cried. He didn't even really _talk_ at all- didn't open up and show me that he trusted me enough to be a little bit vulnerable.

No, he didn't do any of those things. Peeking at him through the curtain of my hair and through my tear-blurred eyes, I saw him struggling with himself though. I could almost _feel_ the invisible force that was pulling him away from all of it- pulling him safely away from the intense, emotional, dramatic, crying girl in front of him. And then I could see him battling his own conflicted thoughts- part of him wanting, no doubt, to cut his losses and _run_; and the other part that still had him standing, stock-still, in front of me.

It felt like forever, but eventually, he took a step toward me. He sat next to me. He said my name, and he told me wasn't going anywhere. He looked like he was trying so hard to say more than that- but he couldn't quite get there.

And at the time, I guess that was enough. I accepted it as the best he could do right then, and I think I had some idea of how much even that had cost him.

He's not used to this. He's not used to people who want to be close to him; he's not used to loving or letting others love him. He's not used to worrying about what someone else needs, and he's not used to giving them those things. Somehow with Jess, isolation and freedom have gotten inexplicably twisted up together, until he feels like he's giving up one if he's giving up the other.

And I understand that about him. But I also understand that I deserve all of those things that he's not capable of giving. That I _need _all of those things.

Some part of me believes he wants to learn to love, though. Learn to love me. And that we can get to that point. And that, even though it might be painful sometimes, sticking with him through this will be so totally worth it in the end.

He's got this uncanny way of making me feel like the whole world's a possibility, if that makes sense. He makes me feel bright and burning and a little bit dangerous. Sort of like standing on the edge of some vast precipice- that thrill of adrenaline you get, knowing that with one misstep you might fall so far down. It puts you on edge, to be sure, but the panoramic, stunning view is awe-inspiring enough that the whole thing still makes you feel you truly _alive_.

So I let him put his arms around me. And I sigh a little as he shifts my weight towards him, and I let myself kind of melt into his warmth. He feels good. He always does... and I think to myself, I could get used to this feeling.

Part of me wants to force a conversation. Part of me wants to clear the air and make him tell me what's going through his head- how he feels about what's happening between us, how he feels about me, how feels about Stars Hollow and Luke and his mother left behind in New York... I want all of it. I want to know him- all of him, every last bit and I'm fighting the urge to still be angry at him for always being so taciturn. Because as much as I'm used to being an open book, he's that used to being closed. And I know that I'm not the only one in this relationship that can be scared off.

Yelling at him for not opening up was probably not the smartest thing to do. But I think I had tried to convey all those things to him already, without getting angry and emotional, and I didn't get much of a response.

Or any response, really. So maybe the yelling was called for. And honestly, sometimes you just can't help an emotional breakdown. We Gilmores tend to be famous for those, every once in a while...

But I guess he got the message. And he didn't run. I'm glad for that. It kind of makes me think that maybe, if we're careful and kind and as honest as we can be in whatever way we can be, that maybe this will work.

I realize I'm wasting this moment over-thinking things and analyzing, in typical Rory Gilmore fashion. So I try to let my thoughts go for a second, and just smile and enjoy the feel of his body next to mine.

And it still feels right.


	5. Shout It From The Rooftops

Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: The last installment in this little ficlet, I think. Let me know how it leaves you feeling. :)

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V. Shout It From The Rooftops

"I couldn't find a rooftop... but I figured I'd go ahead and do the best I could," I stop for a second, wondering if I should say the rest of what I'm thinking; fighting against the natural urge to shut the hell up and close off, I continue. "I guess... you could say it's something I've been working on. Making the most of things. Trying my best. Not just giving up on things," I finish quietly.

The way she's looking at me, I can't tell if she gets it and is happy with my stunted efforts, or if she just thinks I'm crazy and not the Jess she thought I was. We're on the deserted top level of a parking garage, for chrissakes, of _course_ she thinks I'm crazy. I'm starting to think maybe I _should_ have just kept my mouth shut; should've just left well enough alone and not starting looking for buildings with roof access and other alternatives...

It's driving me insane , 'cause she's still just _staring_ and I'm used to being able to read her, or at least used to _her _being the talkative one; anything really so _I'm_ not the one guessing at _her_ feelings.

And yeah, I do appreciate the irony of that. Me being the one in this position and hating every second of it, knowing that I've put her through the same countless times before.

I guess that's part of the point, though. Part of what she was trying to tell me when she broke down at the bridge. And I thought this was a pretty good way to start making amends. To put myself on the line, to put myself out there, to leave myself vulnerable and wondering and not in control.

But fuck if it isn't painful.

"Rory..." I clear my throat. "...What- what are you thinking?" Christ, I am so not used to working on this communication thing.

But she smiles at that. And I can start to see the glimmer of surprise and appreciation and just plain _happy _in her eyes.

Plus, she's leaning forward to kiss me, and that's never really been a bad sign.

It's a short, chaste, sweet kiss, and it somehow just conveys _satisfied_. We're closer now, obviously, and that does something to take my ridiculous nervousness away. And she's still smiling, and the blue of her eyes is still capable of making my heart jump a little. She's stunning in the half-light of the setting sun.

"Jess... as much as I love hearing you say all of that... and I do, I promise... I'm not sure I really get it. The rooftop part I mean," she adds quickly, "Why exactly are we up here?"

Oh. Right. She probably doesn't remember _every_thing she said when she was ranting the other day. I got so caught up in trying to redeem myself, I forgot about that little thing called _context_. Well, never too late to explain...

There's no other way to say this except to say it quietly and seriously and as sincerely as I possibly can - and hope that she knows how much I really do mean it. So I lean my head down even closer to hers and tell her.

"You said that if you made me happy, at all, that I should shout it from the rooftops... And you do. Make me happy. You make me feel... lighter, and... warmer, and more _hopeful_, than I think I've ever felt before. I like you, Rory Gilmore, and I don't want to lose you by being too proud to say it."

Her eyes are glistening a little, but she's still smiling, and it's hard for me to believe my words can mean so much to her. But there's a part of me that's capable of entertaining the idea that maybe she needs me as much as I need her, and that thought is slowly starting to take hold in my head.

Maybe we can be happy together. Maybe we can hold on to this intangible, effervescent feeling that sparks between us.

Hell, I'm willing to try if she is.

"So you found a rooftop?" Her smile's turned teasing now.

"Well, it isn't _exactly_ a rooftop..." I shrug.

"Yeah, but still, not bad, Jess Mariano. Seriously. I'm impressed."

She's trying to hide her smile as she give me an approving look, and I should probably be at least a _little_ irritated with her mocking, but I can't seem to find it in me to be annoyed. She is possibly the most enchanting, endearing girl I've ever met. Half-fairy, half-girl, filled with some kind of magic and an impossible, infinite beauty...

"Yeah?"

"Yeah. I mean, you really pulled out all the stops with this one... and, correct me if I'm wrong, but I _think_ I might have seen a picnic basket in the back seat of your car?"

I'm grinning now, I can't help it, and I pull her to my side as I steer us toward the car.

"You up for a picnic?"


End file.
